EP1692157B1 - Inhibitors of serine proteases, particularly hcv ns3-ns4a protease - Google Patents
Inhibitors of serine proteases, particularly hcv ns3-ns4a protease Download PDFInfo
- Publication number
- EP1692157B1 EP1692157B1 EP04794554.8A EP04794554A EP1692157B1 EP 1692157 B1 EP1692157 B1 EP 1692157B1 EP 04794554 A EP04794554 A EP 04794554A EP 1692157 B1 EP1692157 B1 EP 1692157B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- compounds
- hcv
- formula
- compound
- inhibitor
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 0 CC1*OCC*1 Chemical compound CC1*OCC*1 0.000 description 7
- UJMSIGJDPWZTSQ-UHFFFAOYSA-N CC(C(CC1)N(C)c2c1ccnc2)=O Chemical compound CC(C(CC1)N(C)c2c1ccnc2)=O UJMSIGJDPWZTSQ-UHFFFAOYSA-N 0.000 description 1
- PFPZAGQEMAMYQU-UHFFFAOYSA-N CC(C(CCC1=CN=C2NC)N1C2=O)=O Chemical compound CC(C(CCC1=CN=C2NC)N1C2=O)=O PFPZAGQEMAMYQU-UHFFFAOYSA-N 0.000 description 1
- ZDCFNVUZZKBCNZ-UHFFFAOYSA-N CC(C(CCC1=NN=C2NC)N1C2=O)=O Chemical compound CC(C(CCC1=NN=C2NC)N1C2=O)=O ZDCFNVUZZKBCNZ-UHFFFAOYSA-N 0.000 description 1
- UUSKMQYLNCLFTB-UHFFFAOYSA-N CC(C(CCCC1=CN=C2NC)N1C2=O)=O Chemical compound CC(C(CCCC1=CN=C2NC)N1C2=O)=O UUSKMQYLNCLFTB-UHFFFAOYSA-N 0.000 description 1
- ZDYGFHNEZWLVJP-UHFFFAOYSA-N CC(C(CCCCC1=CN=C2NC)N1C2=O)=O Chemical compound CC(C(CCCCC1=CN=C2NC)N1C2=O)=O ZDYGFHNEZWLVJP-UHFFFAOYSA-N 0.000 description 1
- NPIBNDZRORAITQ-UHFFFAOYSA-O CC(C(CNC1CCCC2NC)[NH+]1C2=O)=O Chemical compound CC(C(CNC1CCCC2NC)[NH+]1C2=O)=O NPIBNDZRORAITQ-UHFFFAOYSA-O 0.000 description 1
- VLXNCVHYBMHBMV-UHFFFAOYSA-N CC(C(N(CSC1)C1C(C)=O)=O)NC Chemical compound CC(C(N(CSC1)C1C(C)=O)=O)NC VLXNCVHYBMHBMV-UHFFFAOYSA-N 0.000 description 1
- GAMYUCUDQAXAIO-UHFFFAOYSA-N CC(C1N(C)Cc2c1cccn2)=O Chemical compound CC(C1N(C)Cc2c1cccn2)=O GAMYUCUDQAXAIO-UHFFFAOYSA-N 0.000 description 1
- NUXQLGXYEWGPDX-UHFFFAOYSA-N CC(C1N(C)Cc2c1ccnc2)=O Chemical compound CC(C1N(C)Cc2c1ccnc2)=O NUXQLGXYEWGPDX-UHFFFAOYSA-N 0.000 description 1
- KDNQAYIIZBVLSB-UHFFFAOYSA-N CC(C1N(C)Cc2c1cncc2)=O Chemical compound CC(C1N(C)Cc2c1cncc2)=O KDNQAYIIZBVLSB-UHFFFAOYSA-N 0.000 description 1
- VXVQBKDRYOXLFB-UHFFFAOYSA-N CC(C1N(C)Cc2c1nccc2)=O Chemical compound CC(C1N(C)Cc2c1nccc2)=O VXVQBKDRYOXLFB-UHFFFAOYSA-N 0.000 description 1
- BZYFFSJCOIASRM-UHFFFAOYSA-N CC(C1N(C)c2ncccc2CC1)=O Chemical compound CC(C1N(C)c2ncccc2CC1)=O BZYFFSJCOIASRM-UHFFFAOYSA-N 0.000 description 1
- OHHQYXYGHPMPPS-UHFFFAOYSA-N CC(C1NCC2C=NOC12)=O Chemical compound CC(C1NCC2C=NOC12)=O OHHQYXYGHPMPPS-UHFFFAOYSA-N 0.000 description 1
- QVUUJUYRYQRNNN-MUFAAYGBSA-N CCC[C@@H](C(NS(c1ccccc1)(=O)=O)=O)NC([C@H](CC1(C2)SCCCS1)N2C([C@H](C(C)(C)C)NC([C@H](C1CCCCC1)NC(c1nccnc1)=O)=O)=O)=O Chemical compound CCC[C@@H](C(NS(c1ccccc1)(=O)=O)=O)NC([C@H](CC1(C2)SCCCS1)N2C([C@H](C(C)(C)C)NC([C@H](C1CCCCC1)NC(c1nccnc1)=O)=O)=O)=O QVUUJUYRYQRNNN-MUFAAYGBSA-N 0.000 description 1
- PQXPKVVSJRGMNN-UHFFFAOYSA-N CNC(C(N(C)Cc1ccccc1)=O)=O Chemical compound CNC(C(N(C)Cc1ccccc1)=O)=O PQXPKVVSJRGMNN-UHFFFAOYSA-N 0.000 description 1
- RSFOFFYRQNKNCB-UHFFFAOYSA-N CNC(CCCC(CCC1)N2C1S(C)=O)C2=O Chemical compound CNC(CCCC(CCC1)N2C1S(C)=O)C2=O RSFOFFYRQNKNCB-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/08—Peptides having 5 to 11 amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Definitions
- the present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents.
- the invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection.
- the invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention.
- the present invention provides a compound selected from: and or a pharmaceutically acceptable salt or mixtures thereof.
- the radical is:
- the radical is:
- the radical is:
- the radical is:
- R 1 is optionally substituted with up to 3 substituents independently selected from J; and wherein up to 3 aliphatic carbon atoms in R 1 may be replaced by a heteroatom selected from O, NH, S, SO, or SO 2 in a chemically stable arrangement.
- Scheme 1 or 2 in combination with scheme 5 above provides another general method for the preparation of certain compounds of formula I.
- Scheme 12 depicts a synthetic route for another P2 of interest.
- Scheme 1 or 2 in combination with scheme 12 above provides a general method for the preparation of compounds of formula I.
- compositions and methods of this invention may also be modified by appending appropriate functionalities to enhance selective biological properties.
- modifications are known in the art and include those which increase biological penetration into a given biological system (e.g., blood, lymphatic system, central nervous system), increase oral availability, increase solubility to allow administration by injection, alter metabolism and alter rate of excretion.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP10183579A EP2361925A1 (en) | 2003-10-10 | 2004-10-08 | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US51015603P | 2003-10-10 | 2003-10-10 | |
US51376803P | 2003-10-23 | 2003-10-23 | |
PCT/US2004/033238 WO2005037860A2 (en) | 2003-10-10 | 2004-10-08 | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP10183579.1 Division-Into | 2010-09-30 |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1692157A2 EP1692157A2 (en) | 2006-08-23 |
EP1692157B1 true EP1692157B1 (en) | 2013-04-17 |
Family
ID=34467967
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP04794554.8A Active EP1692157B1 (en) | 2003-10-10 | 2004-10-08 | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
EP10183579A Withdrawn EP2361925A1 (en) | 2003-10-10 | 2004-10-08 | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP10183579A Withdrawn EP2361925A1 (en) | 2003-10-10 | 2004-10-08 | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
Country Status (14)
Families Citing this family (119)
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AU2001251165A1 (en) * | 2000-04-03 | 2001-10-15 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease |
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TW200510391A (en) * | 2003-04-11 | 2005-03-16 | Vertex Pharma | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
US7176208B2 (en) | 2003-04-18 | 2007-02-13 | Enanta Pharmaceuticals, Inc. | Quinoxalinyl macrocyclic hepatitis C serine protease inhibitors |
US7109172B2 (en) | 2003-07-18 | 2006-09-19 | Vertex Pharmaceuticals Incorporated | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
MY148123A (en) * | 2003-09-05 | 2013-02-28 | Vertex Pharma | Inhibitors of serine proteases, particularly hcv ns3-ns4a protease |
AR045769A1 (es) | 2003-09-18 | 2005-11-09 | Vertex Pharma | Inhibidores de las serina proteasas, particularmente, la proteasa ns3-ns4a del vhc (virus hepatitis c) |
AU2004282148A1 (en) * | 2003-10-10 | 2005-04-28 | Vertex Pharmaceuticals Incoporated | Inhibitors of serine proteases, particularly HCV NS3-NS4A protease |
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-
2004
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- 2004-10-08 RU RU2006115558/04A patent/RU2006115558A/ru not_active Application Discontinuation
- 2004-10-08 CN CN201010183514A patent/CN101857631A/zh active Pending
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- 2004-10-08 EP EP04794554.8A patent/EP1692157B1/en active Active
- 2004-10-08 TW TW093130680A patent/TW200528472A/zh unknown
- 2004-10-08 MX MXPA06004006A patent/MXPA06004006A/es active IP Right Grant
- 2004-10-08 EP EP10183579A patent/EP2361925A1/en not_active Withdrawn
- 2004-10-08 JP JP2006534377A patent/JP2007532474A/ja active Pending
- 2004-10-08 KR KR1020117029638A patent/KR20120010278A/ko not_active Application Discontinuation
- 2004-10-08 WO PCT/US2004/033238 patent/WO2005037860A2/en active Application Filing
- 2004-10-08 KR KR1020067006901A patent/KR20060130027A/ko not_active Application Discontinuation
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Also Published As
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KR20060130027A (ko) | 2006-12-18 |
MXPA06004006A (es) | 2006-06-28 |
WO2005037860A3 (en) | 2005-11-10 |
RU2006115558A (ru) | 2007-11-20 |
US20070161789A1 (en) | 2007-07-12 |
US20050137140A1 (en) | 2005-06-23 |
NZ546663A (en) | 2010-01-29 |
JP2007532474A (ja) | 2007-11-15 |
TW200528472A (en) | 2005-09-01 |
EP2361925A1 (en) | 2011-08-31 |
US8039623B2 (en) | 2011-10-18 |
US7208600B2 (en) | 2007-04-24 |
IL174863A0 (en) | 2008-02-09 |
CA2541634A1 (en) | 2005-04-28 |
WO2005037860A2 (en) | 2005-04-28 |
NO20062101L (no) | 2006-07-05 |
KR20120010278A (ko) | 2012-02-02 |
AU2004282148A1 (en) | 2005-04-28 |
JP2011246487A (ja) | 2011-12-08 |
EP1692157A2 (en) | 2006-08-23 |
CN101857631A (zh) | 2010-10-13 |
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